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Founder Interview

How Chili Piper Reached Cash Breakeven with 5 Products and Customers Like monday.com (Interview with Co-Founder and Co-CEO Alina Vandenberghe)

Interview Date
September 5, 2024
Interviewee
Alina VandenbergheCo-Founder and Co-CEO
Watch
Watch the full interview on YouTube

Company Metrics at Interview Time

Cash Flow

Breakeven

Products (SKUs)

5

Meetings Booked per Quarter

500

Total Funding Raised

$58,000,000

Historical Snapshot

These numbers were reported by Alina Vandenberghe during her live presentation recorded in September 2024 and represent a historical snapshot, not current figures. See Chili Piper’s current numbers.

Key Takeaways

  • 01Chili Piper is cash breakeven as of 2024
  • 02The company runs 5 products: form routing, chat, team handoff, scheduling, and link distribution
  • 03Chili Piper books 500 meetings per quarter using AI-powered account scoring and targeting
  • 04Customers include monday.com and ClickUp
  • 05Alina took over as acting CMO approximately two years before the interview
  • 06The company raised a total of $58,000,000 across four rounds (including $10M in secondary transactions) including a $33,000,000 Series B in February 2021
  • 07Chili Piper uses 300 data-point criteria to qualify and score target accounts
  • 08The company previously built and killed an inbox product after determining switching costs from Gmail and Microsoft were too high
  • 09Alina credits a flat, self-managed org structure as central to operational excellence
  • 10Partner co-marketing, founder brand, ABM, live events, and influencer marketing are the five stated growth tactics

Company Metrics at Time of Interview

MetricValueSource
Cash FlowBreakevenFounder interview, Sep 2024
Products (SKUs)5Founder interview, Sep 2024
Meetings Booked per Quarter500Founder interview, Sep 2024
Total Funding Raised$58,000,000Founder interview, Sep 2024
Series A (Dec 2020)$15,000,000Founder interview, Sep 2024
Series B (Feb 2021)$33,000,000Founder interview, Sep 2024
Secondary Round (Dec 2019)$3,000,000Founder interview, Sep 2024
Secondary Round (Nov 2021)$7,000,000Founder interview, Sep 2024
Account Scoring Data Points300Founder interview, Sep 2024

Growth Breakdown

Profitability

Alina stated that Chili Piper is cash breakeven as of 2024 and continuing to grow. Financial modeling is handled by the company's fractional CFO.

Products

The company has expanded from a single point solution to five SKUs on its demand conversion platform: form routing, chat, team handoff, scheduling, and link distribution. An inbox product was built and later killed because switching costs from Gmail and Microsoft were deemed too high.

Customers

Notable customers named by Alina include monday.com and ClickUp, all cited as users of Chili Piper's demo scheduling product.

Funding

Chili Piper has raised a total of $58,000,000 across four rounds (including $10M in secondary transactions): a $3,000,000 Secondary in December 2019, a $15,000,000 Series A in December 2020, a $33,000,000 Series B in February 2021, and a $7,000,000 Secondary in November 2021.

Growth Strategy

AI-Powered Account Scoring and Targeting

Chili Piper built autonomous AI bots to qualify accounts across 300 data points, including sales rep count, lead volume, sales cycle complexity, and review ratings. This system helped the team book 500 meetings per quarter by focusing outreach on the highest-propensity accounts.

Partner Co-Marketing and Ecosystem Building

Alina described co-marketing events with partners such as Mutiny and credited the Crossbeam platform and its ecosystem playbooks as central to the partner strategy. She framed the goal as elevating partners so that the whole ecosystem wins together.

Founder Brand and Community

Alina is active on LinkedIn and uses her personal brand to build community, asking new connections to write SaaS Open so she can track where relationships originate. She described the outcome as an ecosystem where customers and employees advocate for the product without being prompted.

Influencer Marketing

Chili Piper works with influencers by offering creative value beyond cash, such as helping them grow their audience reach. Alina shared that one influencer generated significant impressions in Q1 without large spend.

Live Events and Account-Based Marketing

In-person events are a deliberate part of the GTM playbook because Alina believes real relationships form faster face to face. ABM is layered on top, with precise pipeline activities tracked against funnel conversion metrics including account touches, velocity, and first engagements.

Best Quotes

In entrepreneurship, only have two modes. Either we're in terror or we're in euphoria.
The most important thing for me when I hire someone in my company is that they have the belief that we can achieve the kind of crazy numbers together, that they believe that we can do it.
We're cash breakeven and we're continuing to grow.
We focused on what we know, which is pipeline conversion, and we created five SKUs that you can see here, form routing, chat, team handoff, scheduling, and link distribution.
That's how we managed to book 500 meetings a quarter.
All your products are super easy to copy. If anybody can just go on and copy your products, autonomous AI bots are gonna be here. But there's something that remains, which is our humanity and our ability to connect with others.
I cannot teach these values. I cannot teach people how to believe and I cannot teach people how to care about others, but I can hire people that have these characteristics.
You become a lot more real when you meet people in person. And that's why I think that there's a lot of power at SaaS Open because you can create a lot of partnerships here.

What Happened Next

This page captures Chili Piper's position as reported by Co-Founder and Co-CEO Alina Vandenberghe at a live SaaS Open presentation in September 2024. At that moment the company was cash breakeven, operating five products, and booking 500 meetings per quarter. For current revenue, headcount, and product updates, visit the Chili Piper company profile on getLatka.

View Chili Piper’s current profile and metrics

Full Transcript

Introduction and Welcome

Nathan Latka

00:00Over the next twenty minutes, she's gonna walk you through all of this. Please help me welcome to the stage, miss Alina Vandenberg of Chile Viper.

Alina Vandenberghe

00:12>> Have fun. Enjoy.

Nathan Latka

00:13Got that right. Right? Point solution day one. Right?

Alina Vandenberghe

00:18>> Yeah. Okay. Alright.

Customers monday.com and ClickUp Use Chili Piper

Alina Vandenberghe

00:20>> Alright. I have to ride the wave of the beautiful demo that monday.com, ClickUp, and Hootsuite have in common. Do you know what they all have in common? Why their demo process is so good? They use Chili Piper.

Gen Z Buying Behavior and Adapting the Playbook

Alina Vandenberghe

00:39>> Right. Irina, talk to you about Gen Z buying differently. I'm going to talk to you about the changes that we're making in our organization so that the Gen Zs can have the best experience working in a SaaS company, but also buying from a SaaS company. Because as she pointed out, the traditional playbooks of, entrepreneurship don't work anymore. And you don't have to do things like me. This is just what has worked for us at Chili Piper.

01:09>> It was what's authentic to us. And I think that's one of the biggest lesson is that you can listen to how people have done it in the past. You can listen to crowd knowledge, but what really can work is what adapts to your values and your beliefs. In my case, what I've experienced is that in entrepreneurship, only have two modes. Either we're in terror or we're in euphoria. And if we have lack of sleep, both of

Entrepreneurship: Terror, Euphoria, and Company Culture

Alina Vandenberghe

01:38>> them get accelerated. I am on very few hours of sleep because last night we went to play poker and we kept going. However, there's something that I really want to optimise for, which is having fun and having euphoria at work because that's what motivates me, that's what drives me, that's what keeps me going. I do not want to run a company by being miserable. And the most important part by building a company is creating a culture

02:09>> that you want to live on forever, that you want to live to your grandchildren, to your children, and that's what I call the company of the future. And the structure of such a company, it comes a lot down to how systems are set up, how employees are being helped to thrive and how growth happens. This is how we are to date. There are lot of things that have happened this year, but we're cash breakeven and we're

02:36>> continuing to grow. And our modeling is courtesy of a famous person in this room, our fractional CFO, Josh. This meme was not created by him, but go listen to him speak about how he accumulated 400,000 followers. But as you know, we're all kind of delusional sometimes and that's how we're projecting our numbers.

Cash Breakeven and Growth Projections

Alina Vandenberghe

02:59>> And in my delusion, I think that there's a better way to do companies. There's a better way to run a company that prepares you for the future. And that is the traditional org chart in which we all have an SVP, a VP, a director, an IC is broken. I believe that the best way to run a company is by having a flat structure. Some of you might have read Paul Graham's essay with founder mode, Brian Chesky,

03:27>> Airbnb. Did anyone read it this week? Yes? A couple of you. So what he's referring to by founder mode is that we're told that we can run our company by hiring great people and get outside of their way. Senior great people, that sounds lovely in theory, in practice, because we're founders and we're very particular about things and because we see a lot of things differently, that doesn't really work. So what has worked for me is by

Flat Org Structure and Founder Mode

Alina Vandenberghe

03:51>> creating a structure where there's self management, people can create plans together. We're all seeing things that I might not be able to. People on the front line see things that are different. We all have a purpose, and the purpose matters a lot. The decision making is not made at the top. I gave out control a long time ago. The decision making is made together. That relieves me of a lot of stress. We bring ourselves fully as

04:19>> we are to work, not with masks, not with things that we don't believe in. And there's fluidity in how we actually take action. But in order to execute, I believe that you have to hire a certain kind of people that believe they can.

04:37>> If somebody comes to work just because they have to do their job, if they do not have a desire to win, they're not going to win. As a result, the most important thing for me when I hire someone in my company is that they have the belief that we can achieve the kind of crazy numbers together, that they believe that we can do it. And this is a hard one to spot in the hiring process. The

05:01>> belief is not enough. The system is not enough. What is critical is a game plan. Like in sports, if you don't have a game plan, you do not win. And that game plan has to be based on numbers. Numbers can sometimes hide reality, but there are numbers that you can rely on in your pipeline that allow you to play the game better than others. And the pipeline numbers do not lie, especially as you're looking at the

05:29>> funnel progression and as you're looking at demand conversion, you can create game plans and activities that impact those numbers. And I gave you an example here from marketing because I took over marketing about two years ago as an acting CMO. And I started getting obsessed with my ICPs, getting obsessed with my targeting, with my account touches, with my velocity, my first engagements. And as Irina was saying, there are 16 touches before somebody comes and buys. And

05:56>> you want to optimize for all of these impressions that your customers are going to see. And as a result, in our marketing plan, we have very precise activities that are going to influence and that we're tracking towards our pipeline conversion.

06:14>> And yes, we started with one product, the one that's used by monday.com and ClickUp and who would suit. But there were a lot of other products that the market never saw. We actually had, at some point, an inbox as well. And the inbox was allowing buyers to see their entire buyer's journey and see who at the company emailed, what they did, and so forth. We killed it because we realized that it's gonna be so hard to

Hiring for Belief and Building a Game Plan on Numbers

Alina Vandenberghe

06:40>> get people to switch from Gmail or Microsoft to another inbox. In the end, we went a DSN to our space. We called the platform demand conversion. We focused on what we know, which is pipeline conversion, and we created five SKUs that you can see here, form routing, chat, team handoff, scheduling, and link distribution, with the goal of cross selling and creating a machine that that creates a pipeline from these other products. My cofounder, who happens to

07:14>> be my husband and also has fancy pants, is going to speak next after me so he can talk to you more about how those multi product strategy works. I'm going to focus on the things that I have split with him, which is operational excellence. And the best way to achieve operational excellence is, I found, using AI. There are a lot of touch points that can be optimized in the funnel without compromising on authenticity. You don't have

07:42>> to send robocallers to book business. You don't have to send fake emails, a million of them that sound all the same. But you can use AI in the process. And we use it for identifying our ICP. We use it for account scoring, for targeting. To give an example, we have a propensity to sell to our companies if they have some of these criteria here, if they have more than 10 sales reps, if they have a high

08:12>> influx of leads, if they have a complex sales cycle, are in good standing, have good git reviews. And it's hard to qualify all these 300 touch points in order to reach out to your best accounts with your best messages. So we created all sorts of bots to ensure that our data points are correct.

08:32>> We also observed that we're going to sell less well if, sorry, they're based in Europe, they take forever to close.

Taking Over Marketing and Obsessing Over ICP

Alina Vandenberghe

08:40>> If they're on Outlook, some reason, that use Outlook, they're a lot slower to make decisions as well than if they are a traditional company. That's how we managed to book 500 meetings a quarter. And I just want to give a shout out for all this AI work that we're doing to Bart's AI for our friend here who has helped us create some of these autonomous AI bots. He's also speaking tomorrow. Know? Alright. Alright. You can just

09:05>> go and chase him, and he can tell you how he does it with his magical team.

09:12>> On top of it, our GTM strategy is probably a lot more unusual because it's the same as day one when we had the point solution. I have not changed any of it. And it comes down to our values, to the way we empower our employees to go to market, and the way we work with the ecosystem. Because by now you all know all your products are super easy to copy. If anybody can just go on and

09:42>> copy your products, autonomous AI bots are gonna be here. They're gonna act as your employees. They can act as salespeople. But there's something that remains, which is our humanity and our ability to connect with others. And that's so much harder to scale and so much harder to fake. And let me tell you how we do it. We have a desire to create a community around us, and I'm not talking about Zendesk or Slack, though we have

Five SKUs and the Demand Conversion Platform

Alina Vandenberghe

10:13>> that too. That's not what I mean by community. What I mean is by having a true, true value of helping people around us. When we hire, when we work with partners, when we work with prospects, when we work with customers, help is really important. When we recruit, I told you that I look at how much they believe that they can succeed. Well, I also look how much they care about helping those around them. Because not everybody

10:41>> has the same value. I cannot teach these values. I cannot teach people how to believe and I cannot teach people how to care about others, but I can hire people that have these characteristics. And hiring people that generally, but generally care about others is very important to me.

10:56>> Because when I look at my employees, I generally care about growing them as well. And I do unusual things, like if I can't find a job in our company that makes them happy, if I don't find the path for them to grow them in my company, I'm going to find them a job outside. And I really go outside of my way to find them a perfect fit.

11:19>> With prospects, I go the same length. I don't trick them into funnels. I don't trick them into downloading some ebooks that nobody reads. I do not trick them with creating content that's fake. I go above and beyond to help them with sharing my experiences, sharing what I found, sharing things that I know that they care about.

11:43>> With our customers, we do not stop at customer deployment. We help them with tactics. And what do people really care about? Succeeding in their job, getting promoted. We help them with their success metrics. We make them so that they're superheroes inside of their organization so that when others talk about them on stage, they're proud about it. We get them on stage. We get them all sorts of opportunities in which they're shining.

12:06>> We also care for them when they are in trouble. If they're sick, we send them chicken soup. If they're giving birth to a new baby, we help them celebrate that as well. Similarly, when we have a partner on board, we don't just do our playbooks with partners. We become creative with how we're going to help them. And this is an example of something that we've done with Mutiny, an event for marketers together. With our influencers, we

Using AI for Account Scoring and Booking 500 Meetings per Quarter

Alina Vandenberghe

12:32>> also look at being creative beyond cash because influencers, they care as much of audience as we all do. And yes, cash is nice. It helps them survive. But being creative and helping them get more reach is a lot more important.

12:50>> Just an example of impressions of one influencer in Q1 to show you the kind of results you can get without spending too much money, without spending too much effort as well. I thought outside of that, because now we have a lot of products that have important cross sells and triggers for us to sell, We work a lot with Crossbeam and this is a book from Bob Moore. If you haven't read it yet, it's a it's a

13:17>> pretty damn book. It's pretty darn good. We're actually part of the book as well. And it shows some of the playbooks that are used to do integrations with partners and how to elevate partners around you to win together.

13:33>> The end result of our efforts to elevate the community around us. This is an example for Nicolas do any of you know him? He publishes these metrics with Mark SalesTech. No? He actually said it to me, Alina, you didn't build the product. You've created an entire industry because it's an ecosystem. It's a community that people crave to be part of. And that's very, very unique. That's very, very unique because you know that everybody around you is

14:05>> an advocate. You don't have to go outside of your way. You don't have to be on stage to evangelize for your product because everybody else does it on your behalf. And who is better to advocate on your behalf than your customers, your employees? They're going to do it better than you. And it's a lot easier if you empower the right nodes in the ecosystem to get the results you want. And in our case, an important piece

14:30>> of the puzzle let me see if I see for some reason it doesn't look. Anyway, an important piece of the puzzle is creating these relationships in person. Because in the in the digital realm, there's some fakeness around it. Yes, you can exchange some notes, but they don't really know who you are. You become a lot more real when you meet people in person. And that's why I think that there's a lot of power at SaaS Open

14:54>> because you can create a lot of partnerships here. You can create a lot of relationships that are going to last a long time after this event. And hopefully, can create business opportunities out of it as well. And that's been my playbook since day one.

15:10>> And because I'm also on social media like Irina, this is my QR code. You can connect with me on LinkedIn. I promise that I will connect as long as you write SAS open when you connect with me. So when you send me a request to connect, just write SAS open so that I know where where we have created this relationship together.